Diethylamine → N,N-diethyl-2-tert-butylbenzamide

HRID 377978

Reaktionsgleichung

Reaktionsgleichung von HRID 377978
[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19]>C(Cl)Cl>[CH2:18]([N:20]([CH2:21][CH3:22])[C:7](=[O:9])[C:6]1[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=1[C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:19]

Komponenten

5

Edukt 3

HCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 136850tert-Butylbenzoic acid (mixed isomers)

Produkt 1

HCID 18630191N,N-diethyl-2-tert-butylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-tert-butylbenzoic acid (4.0 g, 22.5 mmol) in thionyl chloride (8.2 mL, 112 mmol) was stirred at RT for 2 h, then was concentrated three times from carbon tetrachloride to remove all traces of excess thionyl chloride. A solution of diethylamine (4.93 g, 67.4 mmol) in CH2Cl2 (10 mL) was added dropwise over 10 min to an ice water-cooled solution of the crude acid chloride in CH2Cl2 (35 mL). Ten min after addition was complete, the reaction was partitioned between ether and 10% HCl. The ether phase was then washed with sat aq NaHCO3, then was dried (MgSO4), and concentrated to afford a quantitative yield of N,N-diethyl-2-tert-butylbenzamide as an off-white solid. m.p. 38.5-40.5° C.

Aufarbeitung

  1. concentrationwas concentrated three times from carbon tetrachloride
  2. customto remove all traces of excess thionyl chloride
  3. additionTen min after addition
  4. customthe reaction was partitioned between ether and 10% HCl
  5. washThe ether phase was then washed with sat aq NaHCO3
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5b9b4afcacc4431e8b96140b2f013c9a
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028101

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